Jia Jiang wants to write for Bloomberg Businessweek. He has never written for a magazine and doesn’t have an idea for an article, but he still wants to see if we’ll give him a shot. After I tell him “no,” he drives to the University of Texas, Austin, where he plans to pester a professor into letting him lecture a class. In the past month, Jiang has asked a Southwest Airlines flight attendant if he could give the on-board safety announcement and a Domino’s employee if he could deliver pizzas, and he also urged an ice cream shop to invent a flavor just for him. He makes at least one preposterous demand every day, records a video of himself doing it, and posts it on a blog at his website, entresting.com.

His project, 100 Days of Rejection Therapy, is based on the idea that once you’re used to the strange looks, rude comments, and outright dismissal of every thing you’re trying to achieve, you’ll be able to overcome whatever makes you nervous: speaking in public, asking a woman out, or—in Jiang’s case—seeking funding for your tech startup.

“Everybody has failures periodically,” says career coach Marty Nemko. “The people who are generally successful are the ones who bounce right back.” That applies to everyone from the intern who can’t get hired full-time to Steve Jobs, who was once ousted from his own company. “You’ve got to be willing to crash and burn,” Jobs told the Silicon Valley Historical Association in 1994. “If you’re afraid of failing, you won’t get very far.” Jiang, a particularly sensitive entrepreneur, used to be very, very afraid.

Last July, four days before his first child was born, Jiang, 31, quit his job at Dell to follow his dream of “becoming the next Bill Gates.” He’d admired the Microsoft co-founder since he saw Gates speak at Peking University in 1995, when Jiang was 14. He came to the U.S. two years later on a cultural exchange program, studied computer science at Brigham Young University, and moved to Austin after he got his MBA and Dell offered his wife a job. Jiang ended up working there, too, but left after three years to focus on Hooplus, a social networking to-do list app he’s developing. “My wife and I agreed that she’d support the family for six months while I do this. After that, I have to get another job,” he says.

Time’s up this month.

So far, Jiang has launched a website and hired four employees, but finding financial backing has been hard. In November a major investor he’d been courting opted out. Jiang was crushed. “When you invest in a startup, you’re really investing in the people, especially the CEO,” says Jiang. “It wasn’t just that the deal fell through; our team was rejected. It really hurt.”

When Jiang describes the experience, he sounds like someone who was dumped. “I wondered if I should just give up right then,” he says. He was angry and insecure and plagued by a painful, sinking feeling in his stomach. That hurt is real, says Naomi Eisenberger, an assistant professor of social psychology at the University of California, Los Angeles who studies the way emotional trauma activates the same neural pathways that pain does. “Physical pain acts as an alarm system to alert you to a threat,” she says. “We think the pain system was co-opted to highlight the danger of being separated from others, which is also a threat to our survival.” That’s why we sometimes shy away from emotionally painful situations, just as we might avoid a hot pan. To build up resistance, Jiang thought, he’d force himself to get burned.

Jiang started his project on Nov. 15. For his first rejection, he asked a hotel security guard if he could borrow $100. The video of the exchange is awkward and uncomfortable to watch. “No,” the guard says incredulously and then asks why he needs the money. Jiang doesn’t appear to hear him. “No? O.K., thanks,” he mumbles, rushing away. “I was so nervous,” Jiang says a month later, with more than 30 videos completed. “I knew he was going to say ‘no,’ so I just wanted to get it over with.”

Jiang loosened up over subsequent videos and learned the art of the follow-up question. On Day 5, when he asked to tour a grocery store’s warehouse, he did so several times, phrasing his questions in different ways. (The answer was still “no.”) On Day 8, he struck up a conversation with the first person in line outside a Best Buy on Black Friday before asking if he could cut in front. (No way.) Jiang has since gotten more confident and friendly; now, when he asks for crazy things, a number of people answer “yes.” A Krispy Kreme employee agreed to link donuts in the shape of the Olympic rings, and though a one-story firehouse didn’t have a pole for Jiang to slide down, the firefighters did give him a tour of the building. One man even allowed Jiang to play soccer in his backyard. “Knocking on that door was scary,” Jiang says. “You never know what’s going to happen here—it’s Texas.”

It hasn’t been easy coming up with 100 different harebrained schemes. Over two days in December, Jiang tried unsuccessfully to get a free personal training session from a gym and asked several professors at UT’s McCombs School of Business if he could lecture in their classes about entrepreneurship. When they said “no,” Jiang changed his approach and found a communications professor named Joel Rollins, who teaches an undergraduate class on social movements. Jiang explained that his project applied to Rollins’s class because these movements are often initially rejected by society. Rollins seemed intrigued. “I’m open to fitting you in,” he told Jiang. “Contact me after the first of the year, and I’ll see if I can work you into my syllabus.”

On the drive home from UT, Jiang was beaming with success when he spotted a man dancing on the side of the road in a Santa suit, holding a sign for a local smoothie place. Jiang didn’t need to record another rejection that day, but he pulled a U-turn. “Do you mind if I do a dance with you?” he asked the Santa, who taught him how to Dougie.

It takes Jiang two to three hours to complete a rejection and blog about it each day. More than 260,000 people visited his website in the first three weeks of the project. It’s enough of a success that he has to make sure it doesn’t cut into his real work. He still hopes to get Hooplus off the ground, and his wife has agreed to let him extend the trial period a little to see if he can use some of the publicity to his advantage.

With his newfound courage, Jiang says he’ll find an investor. But career coach Nemko suggests Jiang focus on what made the initial investor balk. “I have clients who apply for a number of jobs [and] who get rejected a bunch. They like to brush it off, like, ‘Oh, it’s the economy,’ but I say: ‘Take a look at yourself. Do you need more skills? What’s your employment track record? Are you obnoxious?’” Usually, when we are rejected, Nemko says, it’s about us. “If you’re trying to meet a romantic partner and you’re turned down left, right, and center, maybe you’re ugly. We’re not supposed to say that, but it’s true.”

Whether or not he’s the next Bill Gates, Jiang has discovered through 100 Days of Rejection that he can consistently come up with entertaining ideas—and that there may be more than one path forward. Maybe Hooplus will take off. Perhaps something will come of the UT lecture. Or not. Either way, after a month and a half of “no,” “no way,” and “never,” Jiang no longer feels the sting of that original investor’s rejection. As he puts it: “I feel like I have swagger now.”

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